5,7-Bis-(benzyloxy)-α-(4-(benzyloxy)phenyl)-3-[3,4-di-O-acetyl-α-O-acetyl-α-L-rhamnopyranosyloxyl]-4H-chromen-4-one

Base Information

• Chemical Name: 5,7-Bis-(benzyloxy)-α-(4-(benzyloxy)phenyl)-3-[3,4-di-O-acetyl-α-O-acetyl-α-L-rhamnopyranosyloxyl]-4H-chromen-4-one
• CAS No.: 849938-27-8
• Molecular Formula: C53H48O12
• Molecular Weight: 876.957
• Mol file: 849938-27-8.mol

Synonyms:5,7-Bis-(benzyloxy)-α-(4-(benzyloxy)phenyl)-3-[3,4-di-O-acetyl-α-O-acetyl-α-L-rhamnopyranosyloxyl]-4H-chromen-4-one;3-[[3,4-Di-O-acetyl-6-deoxy-2-O-(phenylMethyl)-α-L-Mannopyranosyl]oxy]-5,7-bis(phenylMethoxy)-2-[4-(phenylMethoxy)phenyl]-4H-1-benzopyran-4

Chemical Property of 5,7-Bis-(benzyloxy)-α-(4-(benzyloxy)phenyl)-3-[3,4-di-O-acetyl-α-O-acetyl-α-L-rhamnopyranosyloxyl]-4H-chromen-4-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 950.121°C at 760 mmHg
• Flash Point: 368.152°C
• PSA: 138.19000
• Density: 1.331g/cm³
• LogP: 9.76940
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

5,7-Bis-(benzyloxy)-α-(4-(benzyloxy)phenyl)-3-[3,4-di-O-acetyl-α-O-acetyl-α-L-rhamnopyranosyloxyl]-4H-chromen-4-one ^*data from reagent suppliers

Safty Information:

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MSDS Files:

Useful:

Technology Process of 5,7-Bis-(benzyloxy)-α-(4-(benzyloxy)phenyl)-3-[3,4-di-O-acetyl-α-O-acetyl-α-L-rhamnopyranosyloxyl]-4H-chromen-4-one

There total 7 articles about 5,7-Bis-(benzyloxy)-α-(4-(benzyloxy)phenyl)-3-[3,4-di-O-acetyl-α-O-acetyl-α-L-rhamnopyranosyloxyl]-4H-chromen-4-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyl bromide (849938-23-4) + 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one (23405-70-1) → 5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)-3-[3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyloxy]-4H-chromen-4-one (849938-27-8)

Guidance literature:

With silver(l) oxide; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/ol0500463

Reference yield:

phenyl 2-O-benzyl-1-thio-α-L-rhamnopyranoside (849938-16-5) → 5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)-3-[3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyloxy]-4H-chromen-4-one (849938-27-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2: 84 percent / Br₂ / CH₂Cl₂ / 1 h / 0 °C

3: 60 percent / Ag₂O / CH₂Cl₂ / 4 h / 20 °C

With dmap; bromine; triethylamine; silver(l) oxide; In dichloromethane;

DOI:10.1021/ol0500463

Reference yield:

phenyl 3,4-di-O-acetyl-2-O-benzyl-1-thio-α-L-rhamnopyranoside (849938-20-1) → 5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)-3-[3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyloxy]-4H-chromen-4-one (849938-27-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Br₂ / CH₂Cl₂ / 1 h / 0 °C

2: 60 percent / Ag₂O / CH₂Cl₂ / 4 h / 20 °C

With bromine; silver(l) oxide; In dichloromethane;

DOI:10.1021/ol0500463

upstream raw materials:

3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyl bromide

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one

phenyl 2-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl 3,4-di-O-acetyl-2-O-benzyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

4',5,7-tri-O-benzyl-kaempferol 3-O-(2''-O-benzyl-α-L-rhamnopyranoside)

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

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